US 12,262,712 B2
Oxime ether compound and application thereof
Xueming Cheng, Liaoning (CN); Haibo Yu, Liaoning (CN); Liang Chen, Liaoning (CN); Hongfei Wu, Liaoning (CN); Geng Sun, Liaoning (CN); Chunxiao Guo, Liaoning (CN); Libao Xu, Liaoning (CN); Jingbo Xu, Liaoning (CN); and Ningning Sun, Liaoning (CN)
Assigned to SHENYANG SINOCHEM AGROCHEMICALS R & D CO., LTD., Liaoning (CN); and JIANGSU YANGNONG CHEMICAL CO., LTD., Jiangsu (CN)
Appl. No. 17/755,625
Filed by SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD., Liaoning (CN); and JIANGSU YANGNONG CHEMICAL CO., LTD., Jiangsu (CN)
PCT Filed Nov. 2, 2020, PCT No. PCT/CN2020/125780
§ 371(c)(1), (2) Date May 3, 2022,
PCT Pub. No. WO2021/088756, PCT Pub. Date May 14, 2021.
Claims priority of application No. 201911065469.2 (CN), filed on Nov. 4, 2019.
Prior Publication US 2022/0400678 A1, Dec. 22, 2022
Int. Cl. A01N 43/78 (2006.01); A01P 1/00 (2006.01); A01P 3/00 (2006.01); C07D 277/40 (2006.01); C07D 277/46 (2006.01); C07D 277/50 (2006.01)
CPC A01N 43/78 (2013.01) [A01P 1/00 (2021.08); A01P 3/00 (2021.08); C07D 277/40 (2013.01); C07D 277/46 (2013.01); C07D 277/50 (2013.01)] 9 Claims
 
1. An oxime ether compound of formula I or a salt thereof:

OG Complex Work Unit Chemistry
wherein:
X is sulfur or oxygen;
Z is selected from hydrogen, and C1-C6 linear or branched alkyls that are unsubstituted or substituted with a substituent selected from halogen, cyano, trifluoromethyl, trifluoromethoxy, hydroxy, nitro, and amino;
A is CN, (C═O)OR1, (C═O)NHR2, or (C═O)NHNH2;
R1 is C1-C8 alkyl;
R2 is hydrogen or C1-C8 alkyl;
W is selected from hydrogen, acetonitrile, C1-C8 alkyl, C1-C8 haloalkyl, C3-C6 cycloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C1-C8 alkoxy C1-C8alkyl, C(═O)R3, C(═O)CH2R3, C(═O)CH2OR3, NO2, OR4, S(O)2R5, N(R6)R7, and N═C(R8)R9;
Q is selected from hydrogen, acetonitrile, C1-C8 alkyl, C1-C8 haloalkyl, C3-C6 cycloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C1-C8 alkoxy C1-C8 alkyl, and C(═O)R3,
or, Q, N and W are connected to N to form a 3-6 membered saturated or unsaturated ring that contains 0-2 heteroatoms selected from N—R10, O, S, and oxidized S optionally substituted by R11 or forms a fused ring with benzene ring;
R3 is selected from hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, C3-C6 cycloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C1-C8 alkoxy C1-C8 alkyl, N(R12)R13, optionally substituted aryl, and optionally substituted heteroaryl;
R4 is selected from hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, and C3-C6 cycloalkyl;
R5 is selected from C1-C2 alkyl, C1-C2 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkyl substituted phenyl, and N(R12)R13;
R6 is hydrogen or C1-C8 alkyl;
R7 is hydrogen or C1-C8 alkyl;
R8 is selected from hydrogen, C1-C8alkyl, C1-C8 haloalkyl, and phenyl that is unsubstituted or optionally substituted by hydrogen, halogen, cyano, nitro, C1-C4 alkyl, or C1-C4 haloalkyl;
R9 is selected from C1-C8 alkyl, C1-C8 haloalkyl, phenyl unsubstituted or optionally substituted by hydrogen, halogen, cyano, nitro, C1-C4 alkyl, or C1-C4 haloalkyl;
R10 is selected from hydrogen, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkylcarbonyl, and C1-C2 alkoxycarbonyl;
R11 is selected from H, halogen, CN, NO2, C1-C2 alkyl, C1-C2 haloalkyl, C1-C4 alkoxy, C1-C2 haloalkoxy, optionally substituted aryl, and S(O)nR14, wherein n is 0, 1 or 2;
R12 is C1-C8 alkyl;
R13 is C1-C8 alkyl; and
R14 is hydrogen, C1-C2 alkyl, C1-C2 haloalkyl, C3-C6 cycloalkyl, and C1-C4 alkoxy.